One of the toughest lessons I had to learn as a businessman was to identify and successfully deal with a no-win situation. That’s a very difficult situation for an entrepreneur to navigate because most of us are optimists by nature. We want to believe we can rescue the relationship, deliver on our promise,s and save the day. But with experience and better understanding of human behavior, I have come to believe that sometimes the best course of action is to cut your losses and walk away before the hole you find yourself in becomes your grave. No one wants to admit failure and throw in the towel too soon, but here are a few scenarios that if you find yourself in, you should consider walking away.

Lost trust. Whether one or both side loses trust, it’s time to call it quits. If you cannot trust your partner, an employee, a vendor, or a client, nothing good can come from the ongoing relationship. The day you come to the realization that “I cannot trust that person,” you need an exit strategy. The sooner you do it, the better.

Unreasonable expectations. High expectations help your product and organization grow to the next level. Unrealistic expectations kill the joy of a project and the spirit of a team, no matter how committed it is. Some clients are unreasonable because they are ignorant of what it takes to get the job done: “it should take you only a few minutes to change the ‘skin’ of our website.”  They can potentially be brought around through education, but they are the exception. Some are unreasonable because they cannot be pleased. “Yes it’s what I wanted but you should have fought me harder on it because I don’t like it now. And you shouldn’t charge me for the changes because I’m not happy.” And then there’s the deadly demanding-ignorant combination, truly a living nightmare.

Ungrateful taker. Historically, the clients to whom I have given the deepest discounts, often at a financial loss, are usually the ones who demand more and more without much appreciation or understanding for the true value of what they’re getting. It amazes me to see that happen over and over again.

In business as well as in life, we need to know when to say enough. I use to think that walking away from a client or a project was a sign of weakness, the mark of a quitter. But today it’s the sign of a wise person who knows that not every relationship is salvageable.

Have you ever faced a no-win situation? What did you do?